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Volumn 14, Issue 1, 2011, Pages 51-63

Synthesis and surface-active properties of uronic amide derivatives, surfactants from renewable organic raw materials

Author keywords

Amide formation; Carbohydrates; Critical micellar concentration; Surface tension; Uronic acid

Indexed keywords

ACID CHLORIDES; ALKYL CHAIN LENGTHS; AMIDE FORMATION; ANOMERS; CHEMICAL SYNTHESIS; CMC VALUES; CRITICAL MICELLAR CONCENTRATIONS; ETHYLENE OXIDES; GLOBAL YIELD; HOMOLOGOUS SERIES; OCTYLPHENOLS; SPECTROMETRIC METHODS; SUGAR-BASED SURFACTANTS; SURFACE-ACTIVE PROPERTY; SYNTHETIC INTERMEDIATES; URONIC ACIDS;

EID: 78651354780     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-010-1205-8     Document Type: Article
Times cited : (22)

References (25)
  • 1
    • 1542430619 scopus 로고
    • Uronic acids: Synthesis and reactions
    • 10.1070/RC1995v064n07ABEH000169
    • VA Timoshchuk 1995 Uronic acids: synthesis and reactions Rus Chem Rev 64 675 703 10.1070/RC1995v064n07ABEH000169
    • (1995) Rus Chem Rev , vol.64 , pp. 675-703
    • Timoshchuk, V.A.1
  • 2
    • 17244382395 scopus 로고    scopus 로고
    • Carbohydrate-alkyl ester derivatives as biosurfactants
    • 1:CAS:528:DyaK1MXkslKhurk%3D 10.1007/s11743-999-0093-4
    • DG Allen BY Tao 1999 Carbohydrate-alkyl ester derivatives as biosurfactants J Surfact Detergents 2 383 390 1:CAS:528:DyaK1MXkslKhurk%3D 10.1007/s11743-999-0093-4
    • (1999) J Surfact Detergents , vol.2 , pp. 383-390
    • Allen, D.G.1    Tao, B.Y.2
  • 3
    • 45449117868 scopus 로고    scopus 로고
    • Recent progress in the synthesis of carbohydrate-based amphiphilic materials: The examples of sucrose and isomaltulose
    • 1:CAS:528:DC%2BD1cXnsFOgt74%3D 10.1016/j.carres.2008.02.008
    • Y Queneau S Chambert C Besset R Cheaib 2008 Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose Carbohydr Res 343 1999 2009 1:CAS:528:DC%2BD1cXnsFOgt74%3D 10.1016/j.carres.2008.02.008
    • (2008) Carbohydr Res , vol.343 , pp. 1999-2009
    • Queneau, Y.1    Chambert, S.2    Besset, C.3    Cheaib, R.4
  • 4
    • 0030114230 scopus 로고    scopus 로고
    • Fractional and structural characterization of wheat straw hemicelluloses
    • 1:CAS:528:DyaK2sXlsVKg 10.1016/S0144-8617(96)00018-5
    • R Sun JM Lawther WB Banks 1996 Fractional and structural characterization of wheat straw hemicelluloses Carbohydr Polym 29 325 331 1:CAS:528:DyaK2sXlsVKg 10.1016/S0144-8617(96)00018-5
    • (1996) Carbohydr Polym , vol.29 , pp. 325-331
    • Sun, R.1    Lawther, J.M.2    Banks, W.B.3
  • 5
    • 0001349147 scopus 로고
    • A survey of the pectic content of nonlignified monocot cell walls
    • 1:CAS:528:DyaL1MXkslWg 10.1104/pp.88.2.309
    • MC Jarvis W Forsyth H Duncan 1988 A survey of the pectic content of nonlignified monocot cell walls J Plant Physiol 88 309 314 1:CAS:528: DyaL1MXkslWg 10.1104/pp.88.2.309
    • (1988) J Plant Physiol , vol.88 , pp. 309-314
    • Jarvis, M.C.1    Forsyth, W.2    Duncan, H.3
  • 6
    • 67649511773 scopus 로고    scopus 로고
    • Impacts of the carbonyl group location of ester bond on interfacial properties of sugar-based surfactants: Experimental and computational evidences
    • 1:CAS:528:DC%2BD1MXntVGjsLw%3D 10.1021/jp903187f
    • H Razafindralambo C Blecker S Mezdour C Deroanne JM Crowet R Brasseur L Lins M Paquot 2009 Impacts of the carbonyl group location of ester bond on interfacial properties of sugar-based surfactants: experimental and computational evidences J Phys Chem B 113 8872 8877 1:CAS:528: DC%2BD1MXntVGjsLw%3D 10.1021/jp903187f
    • (2009) J Phys Chem B , vol.113 , pp. 8872-8877
    • Razafindralambo, H.1    Blecker, C.2    Mezdour, S.3    Deroanne, C.4    Crowet, J.M.5    Brasseur, R.6    Lins, L.7    Paquot, M.8
  • 7
    • 0036354665 scopus 로고    scopus 로고
    • Enzymatically prepared n-alkyl esters of glucuronic acid: The effect of hydrophobic chain length on surface properties
    • 1:CAS:528:DC%2BD38XhsVCht7w%3D 10.1006/jcis.2001.8154
    • C Blecker S Picciuto G Lognay C Deroanne M Marlier M Paquot 2002 Enzymatically prepared n-alkyl esters of glucuronic acid: the effect of hydrophobic chain length on surface properties J Colloid Interface Sci 247 424 428 1:CAS:528:DC%2BD38XhsVCht7w%3D 10.1006/jcis.2001.8154
    • (2002) J Colloid Interface Sci , vol.247 , pp. 424-428
    • Blecker, C.1    Picciuto, S.2    Lognay, G.3    Deroanne, C.4    Marlier, M.5    Paquot, M.6
  • 8
    • 1642302457 scopus 로고    scopus 로고
    • Synthesis of novel d-glucuronic acid fatty esters using Candida antartica lipase in tert-butanol
    • 1:CAS:528:DC%2BD2cXhslChtLw%3D 10.1023/B:BILE.0000018262.57902.68
    • B Moreau G Lognay C Blecker JC Brohée F Chéry P Rollin M Paquot M Marlier 2004 Synthesis of novel d-glucuronic acid fatty esters using Candida antartica lipase in tert-butanol Biotechnol Lett 26 419 424 1:CAS:528:DC%2BD2cXhslChtLw%3D 10.1023/B:BILE.0000018262.57902.68
    • (2004) Biotechnol Lett , vol.26 , pp. 419-424
    • Moreau, B.1    Lognay, G.2    Blecker, C.3    Brohée, J.C.4    Chéry, F.5    Rollin, P.6    Paquot, M.7    Marlier, M.8
  • 10
    • 40949109237 scopus 로고    scopus 로고
    • Enzymatically prepared n-alkyl esters of glucuronic acid: The effect of freeze-drying conditions and hydrophobic chain length on thermal behaviour
    • 1:CAS:528:DC%2BD1cXjvFOht78%3D 10.1016/j.jcis.2008.02.002
    • C Blecker S Danthine M Petre G Lognay B Moreau L Vander Elst M Paquot C Deroanne 2008 Enzymatically prepared n-alkyl esters of glucuronic acid: the effect of freeze-drying conditions and hydrophobic chain length on thermal behaviour J Colloid Interface Sci 321 154 158 1:CAS:528:DC%2BD1cXjvFOht78%3D 10.1016/j.jcis.2008.02.002
    • (2008) J Colloid Interface Sci , vol.321 , pp. 154-158
    • Blecker, C.1    Danthine, S.2    Petre, M.3    Lognay, G.4    Moreau, B.5    Vander Elst, L.6    Paquot, M.7    Deroanne, C.8
  • 12
    • 0342609857 scopus 로고
    • An improved method of synthesis of glucuronamides
    • 1:CAS:528:DyaL3cXlvVKksrs%3D
    • L Falkowski B Stefanska E Bylec P Kolodziejczyk 1980 An improved method of synthesis of glucuronamides Polymer J Chem 54 599 603 1:CAS:528: DyaL3cXlvVKksrs%3D
    • (1980) Polymer J Chem , vol.54 , pp. 599-603
    • Falkowski, L.1    Stefanska, B.2    Bylec, E.3    Kolodziejczyk, P.4
  • 13
    • 84986638414 scopus 로고
    • D-galacturonic acid derivatives with liquid crystalline properties
    • 10.1002/jlac.1992199201192
    • C Vogel U Jeschke V Vill H Fisher 1992 d-galacturonic acid derivatives with liquid crystalline properties Liebiegs Annalen der Chemie 11 1171 1177 10.1002/jlac.1992199201192
    • (1992) Liebiegs Annalen der Chemie , vol.11 , pp. 1171-1177
    • Vogel, C.1    Jeschke, U.2    Vill, V.3    Fisher, H.4
  • 15
    • 0002890621 scopus 로고
    • A method for determination of saccharase activity
    • 1:CAS:528:DyaA2MXhs12qug%3D%3D
    • J Sumner S Howell 1935 A method for determination of saccharase activity J Biol Chem 108 51 54 1:CAS:528:DyaA2MXhs12qug%3D%3D
    • (1935) J Biol Chem , vol.108 , pp. 51-54
    • Sumner, J.1    Howell, S.2
  • 16
    • 0000931046 scopus 로고
    • Application of the quasi-static mode of the drop volume technique to the determination of fundamental surfactant properties
    • 1:CAS:528:DyaK2MXotVOmtbY%3D 10.1006/jcis.1995.1404
    • H Razafindralambo C Blecker S Delhaye M Paquot 1995 Application of the quasi-static mode of the drop volume technique to the determination of fundamental surfactant properties J Colloid Interface Sci 174 373 377 1:CAS:528:DyaK2MXotVOmtbY%3D 10.1006/jcis.1995.1404
    • (1995) J Colloid Interface Sci , vol.174 , pp. 373-377
    • Razafindralambo, H.1    Blecker, C.2    Delhaye, S.3    Paquot, M.4
  • 18
    • 0037126209 scopus 로고    scopus 로고
    • Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group
    • 1:CAS:528:DC%2BD38XntVahtb4%3D 10.1021/ol026629j
    • M Tosin PV Murphy 2002 Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group Org Lett 4 3675 3678 1:CAS:528:DC%2BD38XntVahtb4%3D 10.1021/ol026629j
    • (2002) Org Lett , vol.4 , pp. 3675-3678
    • Tosin, M.1    Murphy, P.V.2
  • 19
    • 18744370755 scopus 로고    scopus 로고
    • Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding
    • 1:CAS:528:DC%2BD2MXjtlWkurk%3D 10.1021/jo0501994
    • M Tosin C O'Brien GM Fitzpatrick H Müller-Bunz W Kenneth Glass PV Murphy 2005 Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding J Org Chem 70 4096 4106 1:CAS:528:DC%2BD2MXjtlWkurk%3D 10.1021/jo0501994
    • (2005) J Org Chem , vol.70 , pp. 4096-4106
    • Tosin, M.1    O'Brien, C.2    Fitzpatrick, G.M.3    Müller-Bunz, H.4    Kenneth Glass, W.5    Murphy, P.V.6
  • 21
    • 0026185429 scopus 로고
    • Chemical modification of hyaluronic acid by carbodiimides
    • 1:CAS:528:DyaK3MXkslaisrw%3D 10.1021/bc00010a007
    • JW Kuo DA Swann GD Prestwich 1991 Chemical modification of hyaluronic acid by carbodiimides Bioconjug Chem 2 232 241 1:CAS:528:DyaK3MXkslaisrw%3D 10.1021/bc00010a007
    • (1991) Bioconjug Chem , vol.2 , pp. 232-241
    • Kuo, J.W.1    Swann, D.A.2    Prestwich, G.D.3
  • 22
    • 49149117202 scopus 로고    scopus 로고
    • Coupling of amines with polyglucuronic acid: Evidence for amide bond formation
    • 1:CAS:528:DC%2BD1cXhtVWksrfJ 10.1016/j.carbpol.2008.02.016
    • N Follain S Montanari I Jeacomine S Gambarelli MR Vignon 2008 Coupling of amines with polyglucuronic acid: evidence for amide bond formation Carbohydr Polymers 74 333 343 1:CAS:528:DC%2BD1cXhtVWksrfJ 10.1016/j.carbpol.2008.02.016
    • (2008) Carbohydr Polymers , vol.74 , pp. 333-343
    • Follain, N.1    Montanari, S.2    Jeacomine, I.3    Gambarelli, S.4    Vignon, M.R.5
  • 23
    • 30744450771 scopus 로고    scopus 로고
    • 1,2,3,4-Tetra-O-acetyl-β-D-glucopyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K
    • 1:CAS:528:DC%2BD2MXht1Oht7fF
    • TC Baddeley RA Howie JMS Skakle JL Wardell 2005 1,2,3,4-Tetra-O-acetyl- β-D-glucopyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K Acta Cryst C61 o711 o714 1:CAS:528:DC%2BD2MXht1Oht7fF
    • (2005) Acta Cryst , vol.61
    • Baddeley, T.C.1    Howie, R.A.2    Skakle, J.M.S.3    Wardell, J.L.4
  • 24
    • 0026040063 scopus 로고
    • A simple method for the microscale preparation of Mosher's acid chloride
    • 1:CAS:528:DyaK38Xht1ygsrw%3D 10.1016/0040-4039(91)80466-J
    • DE Ward CK Rhee 1991 A simple method for the microscale preparation of Mosher's acid chloride Tet Lett 32 7165 7166 1:CAS:528:DyaK38Xht1ygsrw%3D 10.1016/0040-4039(91)80466-J
    • (1991) Tet Lett , vol.32 , pp. 7165-7166
    • Ward, D.E.1    Rhee, C.K.2
  • 25
    • 0034270095 scopus 로고    scopus 로고
    • How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behaviour and the air- water interfacial adsorption of glucose-based surfactants
    • 1:CAS:528:DC%2BD3cXlslGqtb8%3D 10.1021/la991573w
    • B Boyd C Drummond I Krodkiewska F Grieser 2000 How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behaviour and the air- water interfacial adsorption of glucose-based surfactants Langmuir 16 7359 7367 1:CAS:528:DC%2BD3cXlslGqtb8%3D 10.1021/la991573w
    • (2000) Langmuir , vol.16 , pp. 7359-7367
    • Boyd, B.1    Drummond, C.2    Krodkiewska, I.3    Grieser, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.